Stern showed a gift for building consensus, often by tearing others' arguments apart.
"If the general managers are on one side of the discussion, he'll take the other side just to provoke conversation," Kupchak said. "You don't know which side of the conversation he's on until he's done, and then he'll say, 'Well, I'm on your side, I just wanted to hear your argument.' "
There were other times Stern could be just as divisive.
He stubbornly defended the use of a microfiber basketball that cut players' hands before finally relenting two months into the 2006-07 season, and he famously vetoed the trade that would have sent star point guard Paul to the Lakers in 2011.
Kupchak told season-ticket holders in November that he had not forgiven Stern for the Paul decision, but he declined to address the topic last week. "It's gone. It's over," Kupchak said. "I've moved on. There's nothing to say. Don't have time."
Stern also displayed an antagonistic side during two lockouts that forced the cancellation of 48 games per team but resulted in several important victories for owners, including a cap on player salaries and a significant reduction in the players' share of basketball-related income.
"I had many moments with him during union meetings, during lockouts, where he could be just ruthless," said Steve Kerr, the former guard who was a players union representative for the Chicago Bulls. "He's one of those people who was a huge presence and great intelligence and a great command over people and circumstance."
In what was expected to be his final media conference as commissioner this month, Stern, 71, repeatedly poked fun at his successor, deputy commissioner Adam Silver.
When Silver said he anticipated soliciting advice from Stern, his boss told him what to expect upon calling. "It's going to busy," Stern said. "A busy signal."
That might be a first for Stern, who has made a habit of being there when needed for the last three decades.
"I think he's going to go down as probably the greatest commissioner ever in sports," said Kerr, now an analyst for TNT, "when you consider where the league was when he took over, the way he marketed the league and capitalized on the popularity of Magic and Larry [Bird] and Michael and figured out how it should all work in terms of TV contracts and salary caps and marketing.
"He seemed to be ahead of his time before the age of social media. It just felt like the NBA was always sort of two steps ahead of everybody, and I think David Stern has everything to do with that."
To his legion of fans and detractors alike, he was the commissioner who will be remembered as so much more.